Conditioning cellulose acetate yarn



Patented Nov. 9, 1943 CONDITIONING CELLULOSE ACETATE YARN Joseph B. Dickey and James B. Normington, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester; N

New Jersey Y., a corporation of No Drawing. Application December 16, 1938, Serial No. 246,201

,2 Claims. (01. 8-1425 This invention relates to the conditioning of textile yarns and more particularly to the conditioning of filaments and yarns composed of organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate, and cellulose acetate butyrate, to render them more amenable to textile operations such as knitting and the like.

As is well known in the manufacture of yarns, particularly those composed of or containing cellulose organic derivatives, it is necessary to treat the yarn in order to reduce the tendency toward breakage of the individual filaments or fibers when they are subjected to various mechanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. It is also necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is particularly moved from the yarns by the usual scour baths.

A still further object is to provide an improved method for the conditioning of yarns, particularly those composed of or containing organic derivatives of Cellulose such as cellulose acetate, whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs or stitches are employed. Another object is to provide an improved type of yarn which is especially amenable to textile operations including circular important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles and thus produce a closely knit fabric free from such defects as "stitch distortion," pin holes," laddering," and the like.

Heretofore it has been proposed to employ softening agents such as polyhydric alcohols and similar agents as ingredients of yarn conditioning or lubricating formulas, generally in connection with mineral, animal or vegetable oils. It has been found, however, that most of the known softening agents and the various formulas containing them have certain drawbacks, one of the most serious of which is high vapor pressure, and in some cases too drastic a solvent action on the yarn. Many of such agents possess slight or insufllcient solvent power for the lubricants with which they are used, and it is accordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas. In addition, many of the known softening andlubricating agents are insufliciently soluble in water to permit satisfactory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely new class of yarn conditioning agents which are particularly adapted for the treatment of yarns composed of or containing organic derivatives of cellulose and capable of lubrlcating, softening and rendering such yarns knitting, weaving, spinning and the like. Other objects will appearhereinafter.

These objects are accomplished by the following invention which, in its broader aspects, comprises the discovery that compounds having the formula:

where R, R R and R? are the same or different substituted or unsubstituted alkyl, cycloalkyl, aryl or heterocyclic groups and n is 1, 2, 3, etc,, maybe used as yarnconditioning agents and particularly as softening agents, with or without the addition of animal, mineral, or vegetable oils, in the treatment of yarns composed of or containing organic derivatives of cellulose. We have found that these compounds when employed as described in the detailed examples set forth below have slight solvent and/or softening action on cellulose organic derivative yarns which ren-.

der such yarns soft and pliable without at the same time having too drastic an action thereon.

These compounds may be prepared by reacting a tertiary amine containing one or more hydroxyl groups with suitable, organic acids, acid anhydrides, chlorides, etc., to prepare the corresponding ester. Typical examples of organic acids, anhydrides, and chlorides, are acetic acid and acetic anhydride,;aropionic acid and propionic anhydride, propionyl chloride and the like.

pounds of this type are as follows:

Typical examples of compounds which, in ac- Our invention will be more readily undercordance with our invention, we have found to stood by reference to the following examples in be valuable plasticizers, are given in the followwhich typical applications of the invention are ing table. set forth.

DERIVATIVES or Txm'rrmNoLAmrm Compound Formula Boiling range Triethanolamine triacetate N(CaH40C0 CH5); 197-201L7 C./l6 mm,

(CQHAOCOCHS)! Triethanolamine diacetate monopropionate. ]N\ 215223 0.125 mm.

cnnoooclu.

/C2H4OCOCHI Triethanolamine dipropionate monoacetate N 184-187" 0.15 mm.

(OaH 0COC2Hi): Triethanolamine tripropionate N(C-:H4OCOCH5)3....- 2l8-223 C./2l mm, 'lrietbanolamine trihexoato N(C3H0COC5H1])L 210-220 0.]2-3 mm.

Examples of the preparation of the typical com- EXAMPLE 1 Triethanolamine triacetate is applied to textile Preparation of triethanolamine trz'acetate materials (silk, wool, cellulose acetate, cotton,

' viscose, etc.) by means of a Wick, roller, spray 150 parts of triethanolamine are treated with b th, pad, t t fa ilitate their knitting weav 320 parts acetic anhydride. Heat is given off m spinning and the like. If t yam is and the solution is refluxed for two hours. 400 tended primarily for knitting the amount of parts of the triacetate are obtained by distilladitioning liquid applied may vary from 425% tion, having a boiling point b of by weight of the yarn, and if the yarn is intend- 200 C. ed for weaving, the amount of liquid applied may vary between 1-5% by weight of the yarn. Preparatzon of triethanolamine tripromonate EXAMPLE 2 Seven equivalents of propionyl chloride are added slowly to two parts triethanolamine and A Conditioning liquid is made p as fOIIOWSI the whole heated on the water bath until no more Parts hydrogen chloride is given off. The excess acid Triothanolaminemono dipropionateu 0 halide is neutralized with alkali and the tri- Ol ve oil 20 ethanolamine tripropionate obtained 'by distilla- 40 tion in ood ields, havin a boilin oint 218- g y g g p wool, cellulose acetate, viscose, etc., as described 220 C./21 mm.

- in Example 1. If the yarn is intended primarily Preparation of triethanolamine diacetate monoknitting, the amount of conditioning q d 'o t applied may vary fromt 4-25% by weight of the yarn, and if the yarn is intended for weaving, A mixture of 150 parts triethanolamine, '75 the amount of liquid applied may vary between parts propionic acid, 125 parts acetic acid, 5 15% by weight of the yarn. Cellulose acetate parts concentrated sulphuric acid, and parts filaments or fibers treated as described are quite benzene is distilled so that the benzene is auto- 50 soft and pliable and give improved results in varimatically separated from the water and returned ous operations such as weaving, knitting, etc.

and'applied to textile materials such as silk,

to the reaction. Fifty-four parts of water are Other examples of yarn conditioning compocollected. The solution is then washed with disitions which may be applied to various types lute sodium carbonate solution and distilled. of yarn, particularly those composed of or con- Two hundred and eighty parts of the diacetyl, taining cellulose acetate, cellulose acetate promonopropionyl derivative of triethanolamine are pionate, cellulose acetate butyrate, and similar obtained, having a boiling point at 25 mm. of cellulose organic acid esters in accordance with 215-223 C. our invention and which render such yarns soft In accordance with the invention these com and pliable and especially well adapted for varipounds may be applied directly to the yarn durous textile operations, particularly knitting, are as ing or after spinning, or may be added to the follows:

spinning solution itself. We have found that i, 3

these compounds have exceptional solvent pow- Parts ers which enable them to dissolve mineral oils Triethanolamine tripmpionate 80 nd blown and unblown, drying and semi-drying, 5 Blown olive oil 20 vegetable and animal oils and accordingly they may be, and preferably'are, employed as ingre- EXAMPLE 4 dients of yarn conditioning or lubricating for- Parts mulas in conjunction agents which fllIiC- Tripropanolamine dipropionate monoacetate 20 tion wholly or partially as lubricants. Light mineral 11 30 In the following examples and description we have set forth several of the preferred embodi- EXAMPLE 5 ments of our invention, but they are included Parts merely for purposes of illustration and not as a Tributanol amine monovalerate 70 limitation thereof. Blown sperm nil 3o Ethyl di-y-hydroxy propylamino p-methoxy combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.

If the conditioning agent is to be applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll,

or felt wet therewith, or the liquid may be applied by immersion, spray, or otherwise. The

particular point at which the liqui i applied may vary. 'It may, for example, be applied to the yarn inside or outside the spinning cabinet, between the guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In some cases, the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like or by'the so-called bobbin to bobbin method. In the case of staple fiber manufacture, the liquid may be applied to the yarn prior to, or after, cutting into staple lengths.

The amount of the agent so employed will 'vary widely depending upon the results desired,

the specific nature of the material to which the agent is applied, the use to which the yarn is acetate 20 Tetrahydrofurfuryl formate e 20 Blown soya bean oil 60 EXAMPLE 10 A 20% solution of cellulose acetate in acetone, in which is incorporated 1-25% by weight of the cellulose acetate of triethanolamine caproate, is extruded through fine orifices into an evaporative atmosphere. The filaments thus produced are wound or twisted and wound. Yarns thus produced are pliable and suitable for knitting.

, Triethanolamine monobutyratedipropionate Any of the above compositions may be applied to the yarn intended for use in circular knitting by means of a bath, wick, spray, roller, pad or any suitable means. The amount of conditioning liquid applied may vary between 525% by weight of the yarn. Usually, however, the amount of conditioning liquid applied is about 10-15% by weight of the yarn. Yarn composed of cellulose acetate conditioned as described above gives excellent results when used in the circular knitting process.

As will be apparent from the' above examples eventually to be put and other factors. For example, in a given case where a cellulose organic acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.

Although in the above examples we have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, non-solvents, emulsifying agents, blending and the like, may be added within the scope of our invention. Likewise, various dyes or other coloring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

Although we have found it convenient to illustrate our invention by reference to compositions containing specific percentages of the various inredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it and description, the conditioning agents of our invention may be applied by a wide variety-of methods. For example, we may employ the agent as an ingredient of the Spinning dope from which the filaments are formed, the amount of the agent so employed depending upon a number of factors, such as the particular cellulos derivative used in making the yarn, the solvent or solvent is desired to control the solvent or softening action of the conditioning agent, the amount of the agent may be adjusted as, for example, by reducing the amount of the agent and correspondingly increasing the amount of oil or other ingredient.

While we have described our invention with particular reference to the treatment of yarns composed of organic derivatives of cellulose such as celluloseacetate, the conditioning agents and formulas described herein ar applicable to the conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.

The term yam as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of thread, either of high or low twist single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial filaments or a compositethread formed by twisting together individual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filament or threads and spun yarn produced from such stable fibers.

As indicated above, the yarn conditionin agents of our invention are exceptionally good solvents for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such as cottonseed, olive, castor, neat'sfoot, sperm and other oils. This enables them to be used with any of such oils in making up a variety of yarn treating formulas of varying composition. v

The yarn conditioning method and compositions of our invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordance with the invention is their ability to soften yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them soft and pliable and amenable to various textile operations, especially operations such as those involved in weaving and knitting where complicated designs or stitches are employed, without too drastic an action on the eating assistants in conjunction with these oils when applied to such yarns. In addition, due to their solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of our invention as herein described, one is enabled to obtain highly satisfactory results in the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like.

What we claim and desire to secure by Letters Patent of the United States is:

1. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component triethanolamine monoacetate dipropionate.

2. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising triethanolamine mono-acetate dipropionate,

JOSEPH B. DICKEY. JAMES B. NORMINGTON. 

